Taste-modifying combinations

ABSTRACT

The present invention relates to the use of a compound according to formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in the form of any one of its stereoisomers or a mixture thereof, and wherein n is an integer from 0 to 2; 
             the dotted line represents a carbon-carbon single or double bond; and 
             each of R 1  to R 4 , when taken independently from each other, represents a hydrogen atom or represents a R 5  or OR 5  group, R 5  representing a C 1  to C 5 , or even a C 1  to C 3 , alkyl group; and optionally one of the groups R 1  to R 4  represents —OH; and/or 
             when R 1  and R 2  are taken together, and/or R 3  and R 4  are taken together, represent a OCH 2 O group, provided said groups taken together are adjacent substituents of the phenyl group;
 
as an ingredient in combination with other ingredients to confer, enhance, improve or modify the kokumi or umami taste of a flavored article.

CROSS-REFERENCE

This application is a continuation of U.S. patent application Ser. No.14/654,832, which was filed Jun. 22, 2015, which is a 371 national phaseentry of International Application PCT/EP2013/076380, which was filedDec. 12, 2013, which claims the benefit of U.S. Provisional ApplicationNo. 61/745439, which was filed Dec. 21, 2012. The contents of which arehereby incorporated by reference in their entirety.

FIELD

The present invention relates to the field of taste. More particularly,it concerns the use of certain cinnamic acid derived amides astaste-enhancing ingredients to impart or reinforce the tastes known askokumi or umami.

The present invention also concerns compositions or articles containingat least one of the aforementioned compounds.

BACKGROUND

Various cinnamic acid derived amides are known to naturally occur inplants such as Zanthoxylum rubescens (Rutaceae) [Amides from ZanthoxylumRubescens. Adesina, S. K.; Reisch, J. Phytochem. 1989, 3, 839-842.] orPiperaceae [Chemical constituents of peppers (Piper spp.) andapplication to food preservation: naturally occurring antioxidativecompounds. Nakatani, N.; Inatani, R.; Ohta, H.; Nishioka, A., Environ.Health Perspectives 1986, 67, 135-142].

Since vanilloid amides, such as capsaicin or piperine are usually foundin pepper or capsicum species, they generally have a pungent or hottaste. It would be desirable to avoid this. US2003/0152682 (BayerPolymers LLC) and EP 1 323 356 (Symrise) disclose the use of ferullicacid amides as pungent compounds or heat generating-system for oralhygiene products. Included in this document is the compoundtrans-rubenamine, but it is not described or even suggested to have anumami taste. EP 2 138 152 (to Henkel) describes mouthwash compositionscontaining ferrulic acid derived amides among other amides or pungent,or cooling compounds. However, none of these documents anticipate,report or suggest that the compounds described therein have organolepticproperties that can be used to impart or reinforce a kokumi or umamitaste.

In New Developments in Umami (Enhancing) Molecules by Winkel et al,Chemistry & Biodiversity, Vol. 5 (2008), p1195-1203, a review of knownumami modifying compounds is given. However, there is no suggestion ofthe compounds of the present invention.

Kokumi and umami are now established descriptors in the field of tasteand are known to supplement, enhance, or modify the taste and/or aromaof a food without necessarily having a strong characteristic taste oraroma of their own. A desire for kokumi and umami exists for a widerange of foods like soups, sauces, savory snacks, prepared meals,condiments, etc. Moreover, they are often found to complement or enhancefoodstuffs which have a savory or salty characteristic and, as a result,may be useful where sodium or salt reduction is desired.

Umami is one of the five basic tastes sensed by specialized receptorcells present on the human tongue. Umami applies to the sensation ofsavoriness, and particularly to the detection of glutamates and/orribotides which are common in meats, cheese and other protein-richfoods. The behavior of umami receptors explains why foods containingmonosodium glutamate (MSG) often taste “fuller”. However, some consumersare apparently sensitive to MSG and may suffer from headaches or otherillnesses upon consuming it. Thus replacement of MSG, at leastpartially, can be desirable.

Kokumi has been described variously as “deliciousness”, “continuity”,“mouthfulness”, “mouthfeel” and “thickness”. It exists naturally in avariety of foods such as cheese, giving a ‘mature’ cheese taste;vegetable flavors, particularly tomato; meat, where it gives a fullnessand longer lasting taste; mayonnaise & dressings, where it can round outacid notes; fat-reduced food products, where it gives a similar fullnessto full-fat products; herbs and spice; and soups, especially miso soup.

US2006/057268 reports saturated or unsaturated N-alkamide and their useas umami ingredients.

It would be desirable to provide a flavor or taste enhancing ingredientthat has umami or kokumi characteristics. It would be even moredesirable to provide a flavor or taste enhancing ingredient that hasumami and kokumi characteristics.

SUMMARY Provided herein is a taste-modifying composition comprising amixture of at least a compound according to formula (I)

-   -   in the form of any one of its stereoisomers or a mixture        thereof, and wherein n is an integer from 0 to 2;    -   the dotted line represents a carbon-carbon single or double        bond; and each of R¹ to R⁴, when taken independently from each        other, represents a hydrogen atom or represents a R⁵ or OR⁵        group, R⁵ representing a C₁ to C₅, or even a C₁ to C₃, alkyl        group; and optionally one of the groups R¹ to R⁴ represents —OH;        and/or    -   when R¹ and R² are taken together, and/or R³ and R⁴ are taken        together, represent a OCH₂O group, provided said groups taken        together are adjacent substituents of the phenyl group;        as an ingredient in combination with other ingredients to        confer, enhance, improve or modify the kokumi or umami taste of        a flavored article.

DETAILED DESCRIPTION

A taste-modifying composition comprising:

a mixture of:

-   (i) a compound according to formula (I)

-   in the form of any one of its stereoisomers or a mixture thereof,    and wherein n is an integer from 0 to 2;-   the dotted line represents a carbon-carbon single or double bond;    and each of R¹ to R⁴, when taken independently from each other,    represents a hydrogen atom or represents a R⁵ or OR⁵ group, R⁵    representing a C₁ to C₅ alkyl group; and optionally one of the    groups R₁ to R₄ represents —OH; and/or-   when R₁ and R₂ are taken together, and/or R₃ and R₄ are taken    together, represent a OCH₂O group, provided said groups taken    together are adjacent substituents of the phenyl group; and-   (ii) a flavor base wherein the flavor base is selected from the    group consisting of;    -   a) a umami imparting ingredient;    -   b) an acid;    -   c) a salt;    -   d) a sweetness imparting compound; and    -   e) a sweet receptor modulator compound selected from the group        consisting of:

or one of their salts.

In another aspect, provided herein is a method to confer, enhance,improve or modify the taste properties or mouthfeel, as indicated above,of a flavored article, which method comprises adding to the article ataste-modifying compound as described above.

In a particular embodiment, a compound of Formula I one is provided inthe taste-modifying composition in an amount of about 0.1 to about 70%.

In another embodiment, the umami imparting ingredient is provided in thetaste-modifying composition in an amount, by weight, of about 5 to about99%. According to a particular embodiment of the invention, said flavorbase does not comprise another umami imparting flavor ingredient, suchas MSG (mono sodium glutamate), and ribotides (a blend, e.g. 50-50 w/w,of IMP (inosine monophosphate) and GMP (guanosine monophosphate)), forexample in a MSG/ribotides w/w ratio from 95/5 to 90/10.

In another embodiment, the acid is provided in the taste-modifyingcomposition in an amount, by weight, of about 0.1 to about 15%.

In another embodiment, the salt is provided in the taste-modifyingcomposition in an amount, by weight, of about 5 to about 99%.

In another embodiment, the sweetness imparting compound is provided inan amount, by weight, of about 0.2 to about 99%.

In another embodiment, the sweet receptor modulator compounds describedabove is provided in an amount by weight of about 0.2 up to about 99%.

The above taste-modifying compositions can be used as flavors or tasteenhancing ingredients, for instance to impart or reinforce the kokumi orumami taste of a flavor article.

In the context of the present invention “use of a compound of formula(I)” includes the use of any composition containing compound (I) andwhich can be advantageously employed in the flavor industry as activeingredient.

For the sake of clarity, by the expression “any one of itsstereoisomers”, or the similar, it is meant the normal meaningunderstood by a person skilled in the art, i.e. that the invention'scompound can be a pure enantiomer (if chiral) or diastereomer (e.g. thedouble bond is in a conformation E or Z).

For the sake of clarity, by the expression “wherein the dotted linerepresents carbon-carbon single or double bond”, or the similar, it ismeant the normal meaning understood by a person skilled in the art, i.e.that the whole bonding (solid and dotted line) between the carbon atomsconnected by said dotted line is a carbon-carbon single or double bond.

One advantage of the present invention is that the compounds conferumami and/or kokumi taste to a product without detrimentally affectingthe flavor profile of the product.

According to a particular embodiment of the invention, said compound (I)is selected from the group of compounds in which

-   n is 0 or 1;-   the dotted line represents carbon-carbon single or double bond; and-   each of R¹ to R⁴, taken independently from each other, represents a    hydrogen atom or represents a R⁵ or OR⁵ group, R⁵ representing a C₁    to C₅, or even a C₁ to C₃, alkyl group.

According to a particular embodiment of the invention, said compound (I)is selected from the group of compounds in which R₁ and R₂ bothrepresent methoxy groups and n is 1.

According to any one of the above embodiments of the invention, saiddotted line represents a carbon-carbon double bond.

According to a particular embodiment of the invention, said compound (I)is a compound of formula

in the form of any one of its stereoisomers or a mixture thereof, andwherein each of R³ or

R⁴, taken independently from each other, represents a hydrogen atom orrepresents a R⁵ or OR⁵ group, R⁵ representing a C₁ to C₅, or even a C₁to C₃ alkyl group.

According to any one of the above embodiments of the invention, R³represents a hydrogen atom or represents a R⁵ or OR⁵ group, and R⁴represents a R⁵ or OR⁵ group, R⁵ representing a C₁ to C₅, or even a C₁to C₃, alkyl group.

According to any one of the above embodiments of the invention, R³represents a hydrogen atom or represents a R⁵ group, and R⁴ represents aR⁵ or OR⁵ group, R⁵ representing a C₁ to C₅, or even a C₁ to C₃, alkylgroup.

According to any one of the above embodiments of the invention, R³represents a hydrogen atom or represents a R⁵ group, and R⁴ represents aR⁵, R⁵ representing a C₁ to C₅, or even a C₁ to C₃, alkyl group.

According to any one of the above embodiments of the invention, R⁵represents a methyl, ethyl, propyl or iso-propyl group.

The compounds of formula (II) wherein:

-   R³ represents a hydrogen atom or represents a C₁ to C₅, or even a    C₁₋₃, alkyl group or a OR⁶ group, R⁶ representing a C₁ to C₅, or    even a C₂₋₃, alkyl group; and-   R⁴ represents a C₁ to C₅, or even a C₁₋₃, alkyl group or a OR⁶    group, R⁶ representing a C₁ to C₅, or even a C₁₋₃, alkyl group;    are also novel compounds and therefore they represent another aspect    of the invention.

According to any one of the above embodiments of the invention, saidnovel compounds are those wherein R³ represents a hydrogen atom or aC₁₋₃, alkyl group and R⁴ represents a C₁₋₃, alkyl group or OR⁶ group, R⁶representing a C₁ to C₃ alkyl group.

According to any one of the above embodiments of the invention, saidcompound (I) or (II) is a C₁₉₋₂₅ compound, or even a C₁₉₋₂₂ compound.

According to any one of the above embodiments of the invention, thenon-aromatic carbon-carbon double bond of compound (I) or (II) can be ina configuration Z or E or a mixture thereof. According to any one of theabove embodiments of the invention, said compound (I) or (II) is in theform of a mixture of the E and Z stereoisomers, said mixture comprisingat least 50% w/w, or at least 80% w/w, of the stereoisomer E, theremaining being essentially the Z stereoisomer.

According to a particular aspect of the present invention, said compound(I) is selected amongst(E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide (referencedin the Examples as Amide 1),(E)-3-(3,4-dimethoxyphenyl)-N-(3-methoxyphenethyl)acrylamide (referencedin the Examples as Amide 4),(E)-3-(3,4-dimethoxyphenyl)-N-(3-ethoxyphenethyl)acrylamide (referencedin the Examples as Amide 7),(E)-3-(3,4-dimethoxyphenyl)-N-(3-propoxyphenethyl)acrylamide (referencedin the Examples as Amide 8),(E)-3-(3,4-dimethoxyphenyl)-N-(4-isopropoxy-phenethyl)acrylamide(referenced in the Examples as Amide 9),(E)-3-(3,4-dimethoxyphenyl)-N-(4-ethylphenethyl)acrylamide (referencedin the Examples as Amide 10),(E)-3-(3,4-dimethoxyphenyl)-N-(3,4-dimethylphenethyl)acrylamide(referenced in the Examples as Amide 11),(E)-3-(3,4-dimethoxyphenyl)-N-(4-isopropylphenethyl)acrylamide(referenced in the Examples as Amide 12) or(E)-3-(3,4-dimethoxyphenyl)-N-(3-methylphenethyl)acrylamide (referencedin the Examples as Amide 17).

The compounds of the invention can be used alone or in mixtures andprovide a strong kokumi or umami taste at exceptionally low levels.

As mentioned above, the invention concerns the use of a compound offormula (I) as a taste-conferring or enhancing ingredient, and inparticular to impart or reinforce kokumi or umami taste.

According to a particular embodiment of the invention, said compound (I)is used to impart or reinforce kokumi or umami taste as well as toenhance the saltiness and/or savory perception of a flavor.

According to a particular embodiment of the invention, such use is verymuch appreciated by flavorists to impart or enhance the kokumi or umamitaste in savory flavors, such as beef, chicken, pork, and seafood.Surprisingly, in seafood applications such as surimi, or seafoodbouillons or snack flavors, compounds according to formula (I) are alsofound to enhance the perception of sweetness and longevity of theflavor. By contrast, in beef flavors, the compounds according to formula(I) are found to enhance perception of fattiness and tallow notes.Additionally we found that said compounds can increase juiciness in meatbased products.

In another aspect, the invention provides a taste-modifying compositioncomprising:

-   i) as a taste-conferring or modifying ingredient, at least one    compound according to formula (I) above;-   ii) at least one ingredient selected from the group consisting of a    flavor carrier and a flavor base; and-   iii) optionally at least one flavor adjuvant.

By “flavor carrier” we mean here a material which is substantiallyneutral from a flavor point of view, insofar as it does notsignificantly alter the organoleptic properties of flavoringingredients. The carrier may be a liquid or a solid.

Suitable liquid carriers include, for instance, an aqueous system, anemulsifying system, i.e. a solvent and a surfactant system, or a solventcommonly used in flavors. A detailed description of the nature and typeof solvents commonly used in flavor cannot be exhaustive. Suitablesolvents include, for instance, water, propylene glycol, triacetine,triethyl citrate, benzylic alcohol, ethanol, vegetable oils or terpenes.

Suitable solid carriers include, for instance, absorbing gums orpolymers, or even encapsulating materials. Examples of such materialsmay comprise wall-forming and plasticizing materials, such as mono, di-or trisaccharides, natural or modified starches, hydrocolloids,cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteinsor pectins, or yet the materials cited in reference texts such as H.Scherz, Hydrokolloids: Stabilisatoren, Dickungs-und Gehermittel inLebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie,Lebensmittelqualität, Behr's Verlag GmbH & Co., Hamburg, 1996.Encapsulation is a well known process to a person skilled in the art,and may be performed, for instance, using techniques such asspray-drying, agglomeration, extrusion, coacervation and the like.

By “flavor base” we mean here a composition comprising at least oneflavoring ingredient.

Said flavoring ingredient is not a compound of formula (I). Moreover, by“flavoring ingredient” it is meant here a compound, which is used inflavoring preparations or compositions to impart a hedonic effect. Inother words such an ingredient, to be considered as being a flavoringone, must be recognized by a person skilled in the art as being able toimpart or modify in a positive or pleasant way the taste of acomposition, and not just as having a taste.

The nature and type of the flavoring co-ingredients present in the basedo not warrant a more detailed description here, the skilled personbeing able to select them on the basis of its general knowledge andaccording to intended use or application and the desired organolepticeffect. In general terms, these flavoring co-ingredients belong tochemical classes as varied as alcohols, aldehydes, ketones, esters,ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurousheterocyclic compounds and essential oils, and said perfumingco-ingredients can be of natural or synthetic origin. Many of theseco-ingredients are in any case listed in reference texts such as thebook by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair,N.J., USA, or its more recent versions, or in other works of a similarnature, as well as in the abundant patent literature in the field offlavor. It is also understood that said co-ingredients may also becompounds known to release in a controlled manner various types offlavoring compounds.

According to a particular embodiment of the invention, said flavor basecomprises another umami imparting flavor ingredient, such as MSG (monosodium glutamate), and ribotides (a blend, e.g. 50-50 w/w, of IMP(inosine monophosphate) and GMP (guanosine monophosphate)), for examplein a MSG/ribotides w/w ratio from 95/5 to 90/10. Or ingredients rich inthose compounds mentioned before that are well known to the peopleskilled in the art.

Further provided herein is a taste-modifying composition comprising amixture of a compound of Formula I and a flavor base wherein the mixtureis formulated to be added to a foodstuff to provide a flavored article.In another particular embodiment, the taste-modifying compositionmixture is provided in the substantial absence of a foodstuff. Infurther particular embodiment, the taste-modifying composition comprisesless than 2%, particularly less than 1%, more particularly less than0.5%, and more particular less than 0.1%. In a particular embodiment,the taste-modifying composition mixture is provided in the absence of afoodstuff.

In another embodiment, the mixture may be a dry powder.

In another embodiment, a flavored article comprises a compound ofFormula I in an amount of from about 1 to about 100 ppm, moreparticularly from about 10 to about 25 ppm wherein the flavored articlefurther comprises a flavor base wherein the flavor base comprises:

a) a sweetness imparting compound, in amount from about 0.05 to about1000 ppm, particularly from about 0.1 to about 500 ppm. In a particularembodiment the sweetness imparting compound is selected from the groupconsisting of stevia extracts, glycosylated derivatives of steviaextracts (for example, but not limited to, the transglucosylated sweetglycoside mixture of Stevia described in U.S. Pat. No. 7,807,206 andincorporated by reference herein), sugars (for example, but not limitedto, sucrose, glucose, fructose high fructose corn syrup and corn syrup)sucralose, D-tryptophan, NHDC, polyols (sugar alcohols for example butnot limited sorbitol xylitol, and mannitol xylose, arabinose, rhamnoseand lactose), stevioside, Rebaudioside A, thaumatin, mogrosides (forexample but not limited to those present in Luo Han Guo extract),monellin, neotame, aspartame, potassium acesulfame, saccharine,monoammonium glycyrrhizinate, calcium cyclamate, sodium cyclamate,sodium saccharin, potassium saccharin, ammonium saccharin, and calciumsaccharin;

b) an umami imparting ingredient in an amount from about 1 to about 2000ppm, more particularly from about 50 to about 200 ppm. In a particularembodiment when the umami imparting ingredient is ribotide, it is notprovided at 300 ppm in chicken bouillon. In another embodiment, theumami imparting ingredient is selected from the group consisting ofglutamic acid, MSG, ribotides, and ingredients that are sources ofglutamic acid, MSG, ribotides, like yeast extracts, hydrolyzed proteins(for example but not limited to vegetable, corn, and wheat gluten),fermented ingredients, mushroom powder, tomato powder, enzymaticmodified cheese, cheese powders, fish extracts, fermented fish, oystersauce, Worcester sauce, and soy sauce;

c) a salt in an amount from about 100 to about 10,000 ppm. In aparticular embodiment the salt is selected from the group consisting ofsodium chloride, potassium chloride, sea salt, magnesium chloride,calcium chloride, magnesium sulfate, calcium sulfate and a source richin a cations and anions of at least one of the above salts;

d) an acid in an amount from about 1 ppm to about 2000 ppm, moreparticularly from about 50 to about 200 ppm. In a particular embodiment,the acid is selected from the group consisting of tartaric, citric,succinic, tannic, malic, phosphoric, lactic, acetic, ascorbic, anddisodium succinic acids, and sodium lactate.

e) a compound in an amount from about 0.1 ppm to about 200 ppm,particularly from about 0.1 to about 20 ppm, more particularly fromabout 1 to about 15 ppm, wherein the compound is selected from the groupconsisting of:

or one of their salts.

By “flavor adjuvant” we mean here an ingredient capable of impartingadditional added benefit such as a color, a particular light resistance,chemical stability, and so on. A detailed description of the nature andtype of adjuvant commonly used in flavoring bases cannot be exhaustive.Nevertheless, such adjuvants are well known to a person skilled in theart, but it has to be mentioned that said ingredients are well known toa person skilled in the art.

A composition consisting of at least one compound of formula (I) and atleast one flavor carrier represents a particular embodiment of theinvention as well as a flavoring composition comprising at least onecompound of formula (I), at least one flavor carrier, at least oneflavor base, and optionally at least one flavor adjuvant.

In a particular embodiment, more than one compound of formula (I) isused in combination since it is found that a synergistic enhancement ofthe kokumi or umami taste can be achieved in this way. Moreover, it isfound that the combination of ingredients can provide the desired kokumior umami taste without imparting undesirable flavor notes.

Moreover, a compound of formula (I) can be advantageously incorporatedinto flavored articles to positively impart, or modify, the kokumi orumami taste of said articles. Thus, in yet another aspect, the presentinvention provides a flavored article comprising:

-   i) as taste-conferring or modifying ingredient, at least one    compound of formula (I), as defined above, optionally present as    part of a flavoring composition; and-   ii) a foodstuff base.

Suitable foodstuff bases, e.g. foods or beverages, can be fried or not,as well as frozen or not, low fat or not, marinated, battered, chilled,dehydrated, instant, canned, reconstituted, retorted or preserved.Typical examples of said foodstuff bases include:

-   -   a seasonings or condiment, such as a stock, a savory cube, a        powder mix, a flavored oil, a sauce (e.g. a relish, barbecue        sauce, a dressing, a gravy or a sweet and/or sour sauce), a        salad dressing or a mayonnaise;    -   a meat-based product, such as a poultry, beef or pork based        product, a seafood, surimi, or a fish sausage;    -   a soup, such as a clear soup, a cream soup, a chicken or beef        soup or a tomato or asparagus soup;    -   a carbohydrate-based product, such as instant noodles, rice,        pasta, potatoes flakes or fried, noodles, pizza, tortillas,        wraps;    -   a dairy or fat product, such as a spread, a cheese, or regular        or low fat margarine, a butter/margarine blend, a butter, a        peanut butter, a shortening, a processed or flavored cheese;    -   a savory product, such as a snack, a biscuit (e.g. chips or        crisps) or an egg product, a potato/tortilla chip, a microwave        popcorn, nuts, a pretzel, a rice cake, a rice cracker, etc;    -   an imitation products, such as a dairy (e.g., a reformed cheese        made from oils, fats and thickeners) or seafood or meat (e.g. a        vegetarian meat replacer, veggie burgers) analogue; or    -   a pet or animal food.

Particular foodstuffs in which the compound according to formula (I)finds utility include those having topnotes such as seafood, beef,chicken, vegetables, cheese, fat, tallow and/or marrow are important.

For the sake of clarity, it has to be mentioned that, by “foodstuff” wemean here an edible product, e.g. a food or a beverage. Therefore, aflavored article according to the invention comprises one or morecompounds according to formula (I), as well as optional benefit agents,corresponding to taste and flavor profile of the desired edible product,e.g. a savory cube.

The nature and type of the constituents of the foodstuffs or beveragesdo not warrant a more detailed description here, the skilled personbeing able to select them on the basis of his general knowledge andaccording to the nature of said product.

According to any one of the above embodiments of the invention, thetaste-modifying composition and the flavored article according to theinvention comprise as taste conferring or modifying ingredient acompound of formula (II) wherein R³ represents a hydrogen atom orrepresents a R⁵ group, and R⁴ represents a R⁵ or OR⁵ group, R⁵representing a C₁ to C₃ alkyl group. According to any one of the aboveembodiments of the invention, R⁵ represents a methyl, ethyl, propyl oriso-propyl group.

The proportions in which the compounds according to the invention can beincorporated into the various aforementioned articles or compositionsvary within a wide range of values. These values are dependent on thenature of the article to be flavored and on the desired organolepticeffect as well as the nature of the co-ingredients in a given base whenthe compounds according to the invention are mixed with flavoringco-ingredients, solvents or additives commonly used in the art.

In the case of flavoring compositions, typical concentrations are in theorder of 0.05% to 30%, more preferably 0.1% to 20%, most preferably 0.1%to 10%, of the compounds of the invention based on the weight of theflavoring compositions into which they are incorporated. Concentrationslower than these, such as in the order of 0.5 ppm to 300 ppm by weight,more preferably 5ppm to 75ppm, most preferably 8 to 50 ppm, can be usedwhen these compounds are incorporated into flavored articles, thepercentage being relative to the weight of the article.

At these levels the taste is typically described as umami-like, lasting,sweet and lingering.

Additional embodiments of the compositions disclosed herein and the usethereof are also contemplated, wherein the compositions consist of orconsist essentially of the recited components.

EXAMPLES

Embodiments will now be described in further detail by way of thefollowing example, wherein the abbreviations have the usual meaning inthe art, the NMR spectral data were recorded in CDCl₃, with a 400 MHzmachine for ¹H, and a 100 or 125 MHz machine for ¹³C, the chemicaldisplacements, 6, are indicated in ppm with respect to TMS as standard,and the coupling constants, J, are expressed in Hz.

Example 1

Preparation of Compound According to the Invention

Synthesis of Amides with Ethyl Chloroformate, General Procedure:

The acid (E)-3-(3,4-dimethoxyphenyl)acrylic acid (typically 33 mmol) andDIEA (diisopropyl ethyl amine, 2 equiv.) were diluted in 200 mL of EtOAcand 50 mL of dichloromethane. The solution was cooled to 15° C. andethyl chloroformate (1 molar equiv.) was added drop wise. The reactionwas stirred for 1 hour before the starting amine (1 molar equiv.,diluted 2-3 times in EtOAc) was added. The reaction was stirredovernight at room temperature. It was washed with aqueous 5% KHSO₄,brine, aqueous 5% NaHCO₃, brine, and then dried over Na₂SO₄ andevaporated under high vacuum for 3 hours. The crude product was purifiedby flash chromatography (silica gel; cyclohexane/EtOAc, 2:8) or byrecrystallization from EtOAc. Yields were between 50 and 80% on thepurified product.

Amide 1:

Starting Amine: 2-(4-methoxyphenyl)ethanamine

¹H NMR: 2.82 (t, J=7.0, 2H), 3.61 (˜q, J=7.0, 5.9, 2H), 3.78 (s, 3H),3.86 (s, 3H), 3.88 (s, 3H), 5.87 (t, J=5.9, 1H), 6.24 (d, J=15.5, 1H),6.81 (d, J=8.3, 1H), 6.84 (d, J=8.6, 2H), 6.98 (d, J=2.0, 1H), 7.05 (dd,J=8.3, 2.0, 1H), 7.13 (d, J=8.6, 2H), 7.55 (d, J=15.5, 1H).

¹³C NMR: 34.8 (t), 41.0 (t), 55.2 (q), 55.8 (q), 55.9 (q), 109.7 (d),111.1 (d), 114.1 (d), 118.6 (d), 121.9 (d), 127.8 (s), 129.7 (d), 130.9(s), 140.7 (d), 149.1 (s), 150.5 (s), 158.3 (s), 166.2 (s).

Amide 2:

Starting Amine: 2-phenylethanamine

¹H NMR: 2.89 (t, J=6.8, 2H), 3.66 (˜q, J=6.8, 5.5, 2H), 3.87 (s, 3H),3.89 (s, 3H), 5.72 (t, J=5.5, 1H), 6.21 (d, J=15.5, 1H), 6.83 (d, J=8.3,1H), 6.99 (d, J=2.0, 1H), 7.06 (dd, J=8.3, 2.0, 1H), 7.20-7.26 (m, 3H),7.30-7.34 (m, 2H), 7.56. (d, J=15.5, 1H).

¹³C NMR: 35.7 (t), 40.8 (t), 55.9 (q), 55.9 (q), 109.7 (d), 111.1 (d),118.5 (d), 121.9 (d), 126.5 (d), 127.8 (s), 128.7 (d), 128.8 (d), 139.0(s), 140.9 (d), 149.1 (s), 150.6 (s), 166.1 (s).

Amide 3:

Starting Amine: 2-(3,4-dimethoxyphenyl)ethanamine

¹H NMR: 2.84 (t, J=6.9, 2H), 3.63 (˜q, J=6.9, 6.0, 2H), 3.86 (s, 6H),3.87 (s, 3H), 3.89 (s, 3H), 5.79 (t, J=6.0, 1H), 6.23 (d, J=15.5, 1H),6.75 (˜d, J=8.0, 1H), 6.77 (d, J=2.0, 1H), 6.81 (d, J=8.0, 1H), 6.83 (d,J=8.0, 1H), 6.99 (d, J=2.0, 1H), 7.06 (dd, J=8.3, 2.0, 1H), 7.56 (d,J=15.5, 1H).

¹³C NMR: 35.2 (t), 40.9 (t), 55.86 (q), 55.88 (q), 55.93 (2 q), 109.6(d), 111.1 (d), 111.4 (d), 112.0 (d), 118.5 (d), 120.7 (d), 122.0 (d),127.8 (s), 131.4 (s), 140.9 (d), 147.7 (s), 149.1 (s), 149.1 (s), 150.6(s), 166.1 (s);

Amide 4:

Starting Amine: 2-(3-methoxyphenyl)ethanamine

¹H NMR: 2.86 (t, J=6.9, 2H), 3.65 (˜q, J=7.0, 5.7, 2H), 3.79 (s, 3H),3.87 (s, 3H), 3.89 (s, 3H), 5.76 (t, J=5.7, 1H), 6.22 (d, J=15.5, 1H),6.76-6.82 (m, 3H), 6.83 (d, J=8.4, 1H), 6.99 (d, J=2.0, 1H), 7.05 (dd,J=8.4, 2.0, 1H), 7.23 (dt, J=7.5, 1.0, 1H), 7.56 (d, J=15.5, 1H).

¹³C NMR: 35.7 (t), 40.6 (t), 55.2 (q), 55.8 (q), 55.9 (q), 109.7 (d),111.1 (d), 111.9 (d), 114.5 (d), 118.6 (d), 121.1 (d), 121.9 (d), 127.8(s), 129.7 (d), 140.6 (s), 140.8 (d), 149.1 (s), 150.6 (s), 159.8 (s),166.2 (s).

Amide 5:

Starting Amine: 2-(2-methoxyphenyl)ethanamine

¹H NMR: 2.90 (t, J=6.8, 2H), 3.62 (˜q, J=6.8, 5.6, 2H), 3.84 (s, 3H),3.87 (s, 3H), 3.88 (s, 3H), 5.91 (t, J=5.6, 1H), 6.22 (d, J=15.5, 1H),6.82 (d, J=8.3, 1H), 6.87 (˜dd, J=8.4, 1.0, 1H), 6.91 (dd, J=7.5, 1.0,1H), 6.99 (d, J=1.9, 1H), 7.05 (dd, J=8.3, 1.9, 1H), 7.15 (dd, J=7.5,1.8, 1H), 7.22 (dt, J=7.5, 1.8, 1H), 7.53 (d, J=15.5, 1H).

¹³C NMR: 30.3 (t), 39.8 (t), 55.3 (q), 55.8 (q), 55.9 (q), 109.7 (d),110.4 (d), 111.1 (d), 118.9 (d), 120.7 (d), 121.8 (d), 127.4 (s), 127.9(d), 127.9 (s), 130.6 (d), 140.4 (d), 149.1 (s), 150.5 (s), 157.6 (s),166.1 (s).

Amide 6:

Starting Amine: 2-(3,5-dimethoxyphenyl)ethanamine

¹H NMR: 2.82 (t, J=6.9, 2H), 3.64 (˜q, J=6.9, 5.7, 2H), 3.76 (s, 3H),3.87 (s, 3H), 3.88 (s, 3H), 5.85 (t, J=5.7, 1H), 6.24 (d, J=15.7, 1H),6.34 (t, J=2.2, 1H), 6.38 (d, J=2.2, 1H), 6.82 (d, J=8.3, 1H), 6.99 (d,J=2.0, 1H), 7.05 (dd, J=8.3, 2.0, 1H), 7.55 (d, J=15.7, 1H).

¹³C NMR: 36.0 (t), 40.5 (t), 55.3 (q), 55.8 (q), 55.9 (q), 98.4 (d),106.8 (d), 109.7 (d), 111.1 (d), 118.6 (d), 122.0 (d), 127.8 (s), 140.8(d), 141.3 (s), 149.1 (s), 150.6 (s), 161.0 (s), 166.2 (s).

Amide 7:

Starting Amine: 2-(3-ethoxyphenyl)ethanamine

¹H NMR: 1.40 (t, J=7.0, 3H), 2.85 (t, J=6.9, 2H), 3.65 J=6.9, 5.6, 2H),3.88 (s, 3H), 3.89 (s, 3H), 4.02 (q, J=7.0, 2H), 5.70 (t, J=5.6, 1H),6.21 (d, J=15.4, 1H), 6.76-6.81 (m, 3H), 6.83 (d, J=8.3, 1H), 7.00 (d,J=2.0, 1H), 7.06 (dd, J=8.3, 2.0, 1H), 7.20-7.25 (m, 1H), 7.55 (d,J=15.4, 1H).

¹³C NMR: 14.9 (q), 35.7 (t), 40.6 (t), 55.9 (q), 55.9 (q), 63.4 (t),109.7 (d), 111.1 (d), 112.4 (d), 115.1 (d), 118.6 (d), 121.0 (d), 122.0(d), 127.8 (s), 129.7 (d), 140.5 (s), 140.8 (d), 149.1 (s), 150.6 (s),159.2 (s), 166.1 (s).

Amide 8:

Starting Amine: 2-(3-propoxyphenyl)ethanamine

¹H NMR: 1.01 (t, J=7.4, 3H), 1.79 (˜hex, J=7.4, 6.5, 2H), 2.85 (t,J=6.9, 2H), 3.65 (˜q, J=6.9, 5.7, 2H), 3.87 (s, 3H), 3.88 (s, 3H), 3.90(t, J=6.5, 2H), 5.70 (t, J=5.7, 1H), 6.22 (d, J=15.5, 1H), 6.76-6.81 (m,3H), 6.82 (d, J=8.4, 1H), 6.99 (d, J=1.9, 1H), 7.05 (dd, J=8.4, 2.0,1H), 7.19-7.23 (m, 1H), 7.55 (d, J=15.4, 1H).

¹³C NMR: 10.5 (q), 22.6 (t), 35.7 (t), 40.6 (t), 55.8 (q), 55.9 (q),69.5 (t), 109.7 (d), 111.1 (d), 112.5 (d), 115.1 (d), 118.6 (d), 120.9(d), 122.0 (d), 127.8 (s), 129.6 (d), 140.5 (s), 140.8 (d), 149.1 (s),150.6 (s), 159.4 (s), 166.1 (s).

Amide 9:

Starting Amine: 2-(4-isopropoxyphenyl)ethanamine

¹H NMR: 1.32 (d, J=6.1, 6H), 2.81 (t, J=6.9, 2H), 3.61 (˜q, J=6.9, 5.8,2H), 3.87 (s, 3H), 3.88 (s, 3H), 4.51 (hept, J=6.1, 1H), 5.80 (t, J=5.8,1H), 6.23 (d, J=15.5, 1H), 6.81-6.85 (m, 3H), 6.99 (d, J=2.0, 1H), 7.05(dd, J=8.4, 2.0, 1H), 7.11 (˜d, J=8.6, 2H), 7.55 (d, J=15.5, 1H).

¹³C NMR: 22.1 (q), 34.8 (t), 40.9 (t), 55.8 (q), 55.9 (q), 69.9 (d),109.7 (d), 111.1 (d), 116.1 (d), 118.6 (d), 121.9 (d), 127.8 (s), 129.7(d), 130.7 (s), 140.8 (d), 149.1 (s), 150.5 (s), 156.6 (s), 166.1 (s).

Amide 10:

Starting Amine: 2-(4-ethylphenyl)ethanamine

¹H NMR: 1.23 (t, J=7.6, 3H), 2.63 (q, J=7.6, 2H), 2.85 (t, J=6.8, 2H),3.64 (˜q, J=6.8, 5.6, 2H), 3.87 (s, 3H), 3.89 (s, 3H), 5.73 (t, J=5.6,1H), 6.22 (d, J=15.6, 1H), 6.81-6.85 (m, 3H), 6.83 (d, J=8.4, 1H), 6.99(d, J=2.0, 1H), 7.06 (dd,

J=8.4, 2.0, 1H), 7.15 (broad s, 4H), 7.55 (d, J=15.6, 1H).

¹³C NMR: 15.6 (q), 28.4 (t), 35.3 (t), 40.8 (t), 55.8 (q), 55.9 (q),109.7 (d), 111.1 (d), 118.7 (d), 121.9 (d), 127.8 (s), 128.1 (d), 128.7(d), 136.1 (s), 140.7 (d), 142.4 (s), 149.1 (s), 150.5 (s), 166.1 (s).

Amide 11:

Starting Amine: 2-(3,4-dimethylphenyl)ethanamine

¹H NMR: 2.24 (broad s, 6H), 2.82 (t, J=7.1, 2H), 3.63 (˜q, J=7.1, 5.5,2H), 3.87 (s, 3H), 3.88 (s, 3H), 5.75 (t, J=5.5, 1H), 6.22 (d, J=15.6,1H), 6.82 (d, J=8.4, 1H), 6.95 (dd, J=7.7, 1.8, 1H), 6.98-7.00 (m, 2H),7.04-7.08 (m, 2H), 7.55 (d, J=15.6, 1H).

¹³C NMR: 19.3 (q), 19.8 (q), 35.2 (t), 40.8 (t), 55.9 (q), 55.9 (q),109.7 (d), 111.1 (d), 118.6 (d), 121.9 (d), 126.1 (d), 127.9 (s), 129.9(d), 130.1 (d), 134.7 (s), 136.2 (s), 136.8 (s), 140.7 (d), 149.1 (s),150.6 (s), 166.1 (s).

Amide 12:

Starting Amine: 2-(4-isopropylphenyl)ethanamine

¹H NMR: 1.25 (t, J=7.0, 3H), 2.85 (t, J=6.9, 2H), 2.89 (hept, J=7.0,1H), 3.65 (˜q, J=6.9, 5.4, 2H), 3.88 (s, 3H), 3.89 (s, 3H), 5.71 (t,J=5.4, 1H), 6.22 (d, J=15.6, 1H), 6.83 (d, J=8.4, 1H), 7.00 (d, J=2.0,1H), 7.06 (dd, J=8.4, 2.0, 1H), 7.14-7.19 (m, 4H), 7.56 (d, J=15.6, 1H).

¹³C NMR: 24.0 (q), 33.7 (d), 35.3 (t), 40.8 (t), 55.9 (q), 55.9 (q),109.7 (d), 111.1 (d), 118.6 (d), 121.9 (d), 126.7 (d), 127.9 (s), 128.7(d), 136.2 (s), 140.8 (d), 147.1 (s), 149.1 (s), 150.6 (s), 166.1 (s).

Amide 13:

Starting Amine: 2-(3,4-dimethoxyphenyl)ethanamine Starting Acid:(E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic acid

¹H NMR: 2.83 (t, J=7.1, 2H), 3.62 (˜q, J=7.1, 5.9, 2H), 3.858 (s, 3H),3.862 (s, 3H), 5.70 (t, J=5.9, 1H), 5.98 (s, 2H), 6.16 (d, J=15.6, 1H),6.74-6.83 (m, 4H), 6.96-6.97 (m, 2H), 7.56 (d, J=15.6, 1H).

¹³C NMR: 35.2 (t), 40.9 (t), 55.9 (q), 55.9 (q), 101.4 (t), 106.3 (d),108.5 (d), 111.4 (d), 112.0 (d), 118.6 (d), 120.7 (d), 123.8 (d), 129.2(s), 131.4 (s), 140.8 (d), 147.7 (s), 148.2 (s), 149.0 (s), 149.1 (s),166.0 (s).

Amide 14:

Starting Amine: 2-(3,4-dimethoxyphenyl)ethanamine Starting Acid:(E)-3-(4-methoxyphenyl)acrylic acid

¹H NMR: 2.83 (t, J=6.9, 2H), 3.62 (˜q, J=6.9, 5.7, 2H), 3.80 (s, 3H),3.83 (s, 3H), 3.84 (s, 3H), 5.97 (t, J=5.7, 1H), 6.25 (d, J=15.6, 1H),6.73-6.81 (m, 3H), 6.84 (d, J=8.8, 2H), 7.40 (d, J=8.8, 2H), 7.57 (d,J=15.6, 1H).

¹³C NMR: 35.3 (t), 41.0 (t), 55.3 (q), 55.8 (q), 55.9 (q), 111.4 (d),112.0 (d), 114.2 (d), 118.4 (d), 120.7 (d), 127.5 (s), 129.3 (d), 131.5(s), 140.5 (d), 147.7 (s), 149.0 (s), 160.8 (s), 166.3 (s).

Amide 15:

Starting Amine: 2-(3,4-dimethoxyphenyl)ethanamine Starting Acid:(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid. After the Coupling,Deprotection Step was Performed in MeOH/5% aq Na₂CO₃ (1:1)

¹H NMR: 2.83 (t, J=6.9, 2H), 3.63 (˜q, J=6.9, 5.7, 2H), 3.86 (s, 3H),3.87 (s, 3H), 3.90 (s, 3H), 5.63 (t, J=5.7, 1H), 6.17 (d, J=15.4, 1H),6.74 (˜d, J=1.9, 1H), 6.76 (˜dd, J=8.0, 1.9, 1H), 6.82 (d, J=8.0, 1H),6.89 (d, J=8.0, 1H), 6.96 (d, J=1.9, 1H), 7.03 (dd, J=8.2, 1.9, 1H),7.52 (d, J=15.4, 1H). Exchangeable OH not seen.

¹³C NMR: 35.2 (t), 40.9 (t), 55.9 (q), 56.0 (q), 109.6 (d), 111.4 (d),112.0 (d), 114.7 (d), 118.0 (d), 120.7 (d), 122.2 (d), 127.3 (s), 131.4(s), 141.2 (d), 146.7 (s), 147.4 (s), 147.7 (s), 149.1 (s), 166.3 (s).

Amide 16:

Starting Amine: (4-methoxyphenyl)methanamine Starting Acid:(E)-3-(3,4-dimethoxyphenyl)acrylic acid

¹H NMR: 3.79 (s, 3H), 3.87 (s, 3H), 3.89 (s, 3H), 4.49 (d, J=5.7, 2H),5.93 (t, J=5.7, 1H), 6.29 (d, J=15.5, 1H), 6.83 (d, J=8.4, 1H), 6.86(˜d, J=8.7, 2H), 7.00 (d, J=2.0, 1H), 7.06 (dd, J=8.4, 2.0, 1H), 7.24(˜d, J=8.7, 2H), 7.59 (d, J=15.5, 1H).

¹³C NMR: 43.3 (t), 55.3 (q), 55.8 (q), 55.9 (q), 109.7 (d), 111.1 (d),114.1 (d), 118.4 (d), 121.9 (d), 127.8 (s), 129.3 (d), 130.4 (s), 141.1(d), 149.1 (s), 150.6 (s), 159.1 (s), 165.9 (s).

Amide 17:

Starting Amine: 2-(3-methylphenyl)ethanamine Starting Acid:(E)-3-(3,4-dimethoxyphenyl)acrylic acid

¹H NMR: 2.34 (s, 3H), 2.85 (t, J=7.1, 2H), 3.65 (˜q, J=7.1, 5.4, 2H),3.88 (s, 3H), 3.89 (s, 3H), 5.67 (t, J=5.4, 1H), 6.21 (d, J=15.5, 1H),6.83 (d, J=8.3, 1H), 7.00 (d, J=2.0, 1H), 7.02-7.07 (m, 4H), 7.21 (˜d,J=7.5, 1H), 7.55 (d, J=15.5, 1H).

¹³C NMR: 21.4 (q), 35.6 (t), 40.7 (t), 55.9 (q), 55.9 (q), 109.7 (d),111.1 (d), 118.6 (d), 121.9 (d), 125.8 (d), 127.3 (d), 127.8 (s), 128.6(d), 129.6 (d), 138.3 (s), 138.8 (s), 140.8 (d), 149.1 (s), 150.6 (s),166.1 (s).

Example 2 Evaluation of the Umami Effect of the Compound according tothe Invention (In Water)

a) Pure Amide in Pure Water

The amides were evaluated at 20ppm in mineral water in comparison with0.05% monosodium glutamate (MSG). The trained panelists (5-10) weregiving an umami taste intensity note. The Relative umami intensity (RUI)was calculated as follows:RUI=(umami intensity of the amide)/(umami intensity of MSG)*10

The following table gives the average of the notes obtained from allpanelists.

Amide N^(o) 1 2 3 4 5 6 7 RUI 5.6 3.8 3.3 10.2 3.2 3.7 9.8 Amide N^(o) 89 10 11 12 14 17 RUI 9.9 6.5 11.5 13.3 5.9 3.8 12.1

b) In the Presence of Maltodextrin and MSG

Amides 1, 3, 4 and 8 were blended and diluted in maltodextrin at 10%w/w.

Each blend was then added into a water solution containing MSG at 500ppmin order to achieve a concentration ranging between 20 and 100ppm of theamides, as indicated in the tables below:

Sol 1 Sol 2 Sol 3 Sol 4 Sol 5 Sol 6 Sol 7 MSG 500 500 500 500 500 500500 Amide 1 — — — —  20 — — Amide 3 —  20  35  50 — — — Amide 4 — — — ——  20 — Amide 8 — — — — — —  20and also:

Sol 8 Sol 9 Sol 10 Sol 11 Sol 12 Sol 13 MSG 500 500 500 500 500 500Amide 7  20 — — — — — Amide 9 —  20 — — — — Amide 10 — —  20 — — — Amide11 — — —  20 — — Amide 12 — — — —  20 — Amide 17 — — — — —  20 Sol =solution

A panel consisted in 15 to 20 trained panelists evaluating the samplesfor taste properties on a scale of −5 to 5 (−5 denoted no umami effectand 5 denoted extremely strong umami effect, 0 being the umami intensityof a reference umami solution containing Monosodium Glutamate at 0.05%).

The samples were evaluated with and without nose clip to focus on taste.

Umami Umami intensity intensity Description with without Withnose-clip/without nose-clip nose-clip nose-clip Solution 1 0 0 UmamiSolution 2 0.91 0.76 Umami, mouthfeel, salivating/nutty, woody Solution3 0.46 0.65 Umami, mouthfeel, salty/nutty, woody Solution 4 0.95 0.95Umami, salty, mouthfeel, salivating, astringent, metallic/nutty, earthySolution 5 1.13 1.25 Umami, salty, sweet, mouthfeel, fatty Solution 61.72 1.71 Umami, mouthfeel, salty, sweet/nutty Solution 7 1.25 1.46Umami, salty, mouthfeel, salivating, hot, cooling Solution 8 1.27 1.34Umami, sweet, salty, astringent, bitter, mouthfeel Solution 9 0.98 1.16Umami, sweet Solution 10 0.88 0.94 Umami, sweet, salty, pungent, bitterSolution 11 0.8 0.95 Umami, green, herbal, salivating Solution 12 0.951.13 Umami, salty, sweet, herbal, astringent, metallic Solution 13 1.571.47 Umami, salty, pungent, mouthfeel, herbal

Example 3 Evaluation of the Umami Effect of the Compound according tothe Invention (In Applications)

1) Evaluation of Amides 1 and 3 in a Beef Bouillon

A beef stock was prepared containing the following ingredients:

Ingredients in % w/w Maltodextrin 52 Onion Powder 1.5 Salt 32.7 Whitepepper 0.1 Yeast extract 3.8 Palm Oil 7.6 Caramel Color 0.7 Beef flavor1.5

10 g of beef stock was poured in 500 ml of boiling water. MSG and amides1 and 3 were added to the beef bouillon at the dosages indicated inTable 1.

TABLE 1 Ingredients in ppm Bouillon 1 Bouillon 2 Bouillon 3 Bouillon 4MSG — 700 — — Amide 1 — — — 25 Amide 3 — — 50 —

The bouillons were presented to 5 trained panelists on a blind testbasis. They were asked to rate the samples for taste properties on ascale of 0 to 10 (0 denoted no umami effect and 10 denoted extremelystrong umami effect). The results are reported herein below:

TABLE 2 Averages for each bouillon and descriptors Umami intensityComments Bouillon 1 2.1 Yeasty, oniony, beef fat, flat Bouillon 2 5.1More salty, round, umami, oniony, juicy, fatty Bouillon 3 3.1 Mouthfeel,salty, body Bouillon 4 3.9 Umami, round

2) Evaluation of Amide 1 in a Chicken Bouillon

A chicken stock was prepared containing the following ingredients:

Ingredients in % w/w Chicken meat powder 2.5 Maltodextrin 32.2 Garlicpowder 0.5 Palm oil 5 Ground white pepper 0.3 Yeast extract 10 Onionpowder 3.25 Toasted onion powder 2 Turmeric 0.25 Salt 35 Chicken fat 5Chicken flavor 4

10 g of chicken stock was poured in 500 ml of boiling water. MSG andamide 1 were added to the chicken bouillon at the dosages indicated inTable 3.

TABLE 3 Ingredients in ppm Bouillon 1 Bouillon 2 Bouillon 3 MSG — 500 —Amide 1 — — 20

The bouillons were presented to 5 trained panelists on a blind testbasis as described above. The results are reported herein below:

TABLE 4 Averages for each bouillon and descriptors Umami intensityComments Bouillon 1 3.5 Flat, salty Bouillon 2 6.4 Umami, mouthfeel,sweet, pleasant Bouillon 3 6.3 Umami

3) Evaluation of Amides 1 and 4 in a Pork Flavor

Amides 1 and 4 were evaluated at 20 ppm by 5 trained panelists in a porkflavor on a blind test basis as described above. The results arereported herein below:

TABLE 5 Averages for each bouillon and descriptors Umami intensityComments Pork flavor 4.5 Meaty, pork, animalic, fatty, mouthfeel,balanced, good Pork flavor + 6 More umami, more meaty, pork notes Amide1 enhanced, liquorice note, slightly cooling, fatty Pork flavor + 7 Moreumami, rich strong meaty and pork Amide 4 notes, fatty

4) Evaluation of Amides 1, 4, 8, 11, 12 in a Chicken Bouillon ContainingMSG and Ribotides

A chicken bouillon was prepared containing the following ingredients:

Ingredients in % w/w Salt 27 MSG 10 Ribotides 0.03 Sugar 4 Vegetable oil2 Chicken fat 2 White pepper powder 0.1 Yeast powder 1.5 Soy saucepowder 0.5 Chicken powder 4 Maltodextrin 35.77 Corn starch 5 Wheatpowder 3 Egg powder 4 Chicken flavor 1.1

1 g of chicken bouillon was poured into 100 ml of boiling water. Amides1, 4, 8, 11, 12 were added to the chicken bouillon at the dosagesindicated in Table 6:

TABLE 6 Ingredients in ppm Bouillon 1 2 3 4 5 6 Amide 1 — 25 — — — —Amide 4 — — 25 — — — Amide 8 — — — 8 — — Amide 11 — — — — 5 — Amide 12 —— — — — 25

The bouillons were presented to 5 trained panelists on a blind testbasis as described above. The results are reported herein below:

TABLE 7 Averages for each bouillon and descriptors Umami intensityComments Bouillon 1 5.3 White meat, round, no off notes Bouillon 2 6.3Sweet, meaty, balanced, very round, full Bouillon 3 6.3 Slow build,mouthfeel, sweet, umami, no off note, round, very balanced Bouillon 46.7 Strong umami, sweet, lingering, sweet and umami Bouillon 5 6.7 Whitemeat, slightly astringent, very full, round, lasting, no off notesBouillon 6 6 Mouthfeel, no off note, umami, sweet, very balancedslightly astringent

5) Evaluation of Amides 1 and 3 in Marinated Chicken

A marinade was prepared containing the following ingredients:

Ingredients in % w/w Water 90 Salt 4 Hamine phosphate 1 Chicken WhiteMeat Flavor 5

MSG, amides 1 and 3 were added to the marinade at the dosages indicatedherein below:

Ingredients in % w/w Marinade 1 Marinade 2 Marinade 3 Marinade 4Marinade 100 100 100 100 MSG — 0.3 — — Amide 1 — — 0.05 — Amide 3 — — —0.05

Marinades were added with chicken meat in plastic bags in the followingquantities:

Ingredients in % w/w Marinated Marinated Marinated Marinated chicken 1chicken 2 chicken 3 chicken 4 Chicken meat 90 90 90 90 Marinade 1 10 — —— Marinade 2 — 10 — — Marinade 3 — — 10 — Marinade 4 — — — 10

Samples were tumbled under vacuum for 25 minutes, and then cooked in asteam oven until meat temperature reaches 75° C. Samples were thenfrozen and reheat for 20 minutes at 80° C. in the oven beforeevaluation.

The marinated chicken samples were presented to 5 trained panelists on ablind test basis as described above. The results are reported hereinbelow:

TABLE 8 Averages for each marinated chicken and descriptors Umamiintensity Comments Marinated chicken 1 1.3 dry Marinated chicken 2 4Strong, clean, pleasant aftertaste, juicy Marinated chicken 3 4.9 Verysimilar to MSG, meaty, round, brothy, balanced, sweet, full Marinatedchicken 4 3 Clean, pleasant, strong impact, enhances chicken juicy,sweet

6) Evaluation of Amides 1 and 3 in Surimi

Surimi was prepared using the following ingredients in % w/w:

Ingredients in % w/w Frozen surimi base 39.8 Salt 1.19 Native WheatStarch 4.98 Potato Starch 4.98 Sunflower Oil 4.98 Egg White 6.97 Ice36.6 Crab extract 0.5

The dry ingredients (salt, starches) were first put in a bowl chopper.The ice mix was added until homogenous. The surimi base was then addedand mixed for 3 minutes. The oil was added while mixing, followed by theegg white.

MSG and the amides 1 and 3 were added to the surimi preparation at thedosages indicated herein below:

Surimi 1 Surimi 2 Surimi 3 Surimi 4 MSG — 5000 ppm — — Amide 1 — — 50ppm — Amide 3 — — — 50 ppm

The 4 surimis were put in cooking bags and cooked for 45 minutes in asteam oven at 90° C. The samples were then quickly cooled down.

The surimi samples were presented to 5 trained panelists on a blind testbasis as described above. The results are reported herein below:

TABLE 9 Averages for each surimi and descriptors Umami intensityComments Surimi 1 2.2 Flat, eggy, slightly amine, not really fishySurimi 2 5.3 Sweet, umami, round, sweet, salty Surimi 3 3.2 Slightlysweet, umami, juicy, round, fishy, crab Surimi 4 3.7 Crab, slightlyamine, sweet, fishy, oyster, crab, juicy

Example 4

Monosodium glutamate (MSG), amide 1, an ingredient (glucosylated steviaglycosides from U.S. Pat. No. 7,807,206 (containing Rebaudioside A andstevioside), sea salt, succinic acid, yeast extract, hydrolyzed cornprotein, or hydrolyzed wheat gluten) and a blend of the amide with theingredient were weighed and hot mineral water was added to each sampleaccording to the dosages indicated in each experiments. The samples werestirred in order to ensure the solubilisation of the ingredients.

Each sample was coded, and tasted in a random order by 5 trainedpanelists.

For each sample, the umami intensities were rated on a 1-10 scale (1denoted no umami effect and 10 denoted extremely strong umami effect).The “liking” was also rated on a 1-10 scale (1 was given if the samplewas not liked, and 10 liked very much). The panelists were also asked todescribe the samples.

TABLE 10 Amide 1 & glucosylated stevosides Samples Umami LikingPanelists' Comments MSG @ 0.04% 5.8 6.3 Balanced, meaty, up front umamiAmide 1 @20 ppm 4.8 4.8 strong umami, lingering, slow build upglucosylated 1.8 2.8 weak stevosides @8 ppm Amide 1 @20 ppm + 4.6 5.0The sweetest, very long Rebaudioside A lasting, build, umami, @8 ppmclean, the closest to MSG

TABLE 11 Amide 1 with Sea Salt Sample Umami Liking Panelists' CommentsMSG @0.04% 5.8 6.8 immediate onset, umami, balanced, clean Amide 1 @20ppm 3.3 3.8 umami, clean, lasting Sea Salt @0.03% 1.0 1.4 astringent,empty, weak. Amide 1 @20 ppm + 4.1 5.0 umami, slow build, Sea Salt@0.03% lingering, lasting.

TABLE 12 Amide 1 with Succinic Acid (36 ppm) Sample Umami LikingPanelists' Comments MSG @0.04% 4.2 5.8 umami, first impact, meaty, Amide1 @20 ppm 3.7 4.0 umami, lasting, builds Succinic acid @36 ppm 1.0 1.3weak, astringent, Amide 1 @20 ppm + 3.6 5.0 lasting, builds, umamiSuccinic acid @36 ppm up front

TABLE 13 Amide 1 with Yeast Extract (60 ppm) Sample Umami LikingPanelists' Comments MSG @0.04% 5.5 5.8 lasting, umami, round, mouthfeelAmide 1 @20 ppm 4.5 4.3 lingering, slow build up, strong umami, lasting.Yeast extract @60 ppm 3.4 2.2 yeasty, weak, watery, umami. Amide 1 @20ppm + 5.4 5.0 long lasting, builds, Yeast extract @60 ppm lingering,strong umami, sweet, meaty, yeasty

TABLE 14 Amide 1 with Yeast Extract (175 ppm) Sample Umami LikingPanelists' Comments MSG @0.04% 5.5 6.3 strong umami, balanced meaty goodAmide 1 @20 ppm 4.5 3.0 builds, umami, clean, astringent Yeast extract@175 ppm 3.3 3.5 yeasty, umami, balanced, meaty Amide 1 @20 ppm + 6.36.0 strong, build, lasting, Yeast extract @175 ppm yeasty, more meaty

TABLE 15 Amide 1 with Yeast Extract (10 ppm) Sample Umami LikingPanelists; Comments MSG @0.04% 4.0 4.8 mild umami, up front, weak,lingers, round, mouthfeel Amide 1 @10 ppm 2.5 2.5 build, lasting, stronglingering, sl M/F Yeast extract @60 ppm 1.0 3.8 weak Amide 1 @10 ppm +3.8 4.7 builds, lasting, lacks up Yeast extract @60 ppm front, weakmouthfeel, builds slowly, meaty

TABLE 16 Amide 1 with Hydrolized Corn Protein (ppm) Sample Umami LikingPanelists' Comments MSG @0.04% 5.4 5.2 umami, round, mouthfeel, meatyAmide 1 @20 ppm 4.2 3.8 lasting, builds, strong umami, clean Hydrolizedcorn 2.0 1.8 weak protein @40 ppm Amide 1 @20 ppm + 7.3 7.5 lasting,very strong Hydrolized corn umami, and round, protein @40 ppm clean,meaty

TABLE 17 Amide 1 with Hydrolized Corn Protein (320 ppm) Sample UmamiLiking Panelists' Comments MSG @0.04% 3.0 3.7 umami, clean, sweet, full,mouthfeel, round Amide 1 @20 ppm 1.7 3.3 builds slowly Hydrolized corn2.3 3.3 weak, sl umami, umami protein @320 ppm balanced but weak meaty,mild mouthfeel, round Amide 1 @20 ppm + 5.0 4.7 Umami, MSG like, strongHydrolized corn umami impact, lingering, protein @320 ppm bit moreintense, lasting

TABLE 18 Amide 1 with Hydrolized Wheat Gluten (320 ppm) Sample UmamiLiking Panelist's Comments MSG @0.04% 5.5 6.3 mild mouthfeel, round,mild umami Amide 1 @20 ppm 4.0 4.8 lingering umami Hydrolized wheat 2.02.8 very weak mouthfeel, gluten @100 ppm sweet little umami Amide 1 @20ppm + 6.5 5.8 slow builds of mouthfeel, Hydrolized wheat stronger umami,sweet gluten @100 ppm

TABLE 19 Amide 1 with Hydrolized Wheat Gluten (100 ppm) Sample UmamiLiking Panelists' Comments MSG @0.04% 7.2 7.0 more umami and longlasting, umami Amide 1 @10 ppm 3.7 4.5 umami Nature Pep 971481 4.3 5.0yeasty @100 ppm Amide 1 @10 ppm + 5.3 5.5 yeasty and acidic, Nature Pep971481 more umami lingers @100 ppm

In some instances, the combinations provide an umami taste improvementbetter than each component alone. In other instances, the combination ispreferred over each alone.

What is claimed is:
 1. A taste-modifying composition comprising: (i) acompound according to formula (II):

R³ represents a hydrogen atom or represents a R⁵ group, and R⁴represents a R⁵ or OR⁵ group, R⁵ representing a C₁ to C₅ alkyl group;and (ii) glucosylated steviol glycosides or rebaudioside A.
 2. Thetaste-modifying composition of claim 1, wherein the compound of formula(II) is (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide,(E)-3-(3,4-dimethoxy-phenyl)-N-(3-methoxyphenethyl)-acrylamide,(E)-3-(3,4-dimethoxyphenyl)-N-(3-ethoxy-phenethyl)acrylamide,(E)-3-(3,4-dimethoxyphenyl)-N-(3-propoxyphenethyl)acrylamide,(E)-3-(3,4-dimethoxyphenyl)-N -(4-isopropoxyphenethyl)acrylamide,(E)-3-(3,4-dimethoxyphenyl)-N-(4-ethylphenethyl)-acrylamide,(E)-3-(3,4-dimethoxyphenyI)-N-(3,4-dimethylphenethyl)acrylamide,(E)-3-(3,4-dimethoxyphenyI)-N-(4-isopropyl-phenethyl)acrylamide, or(E)-3-(3,4-dimethoxyphenyl)-N-(3-methylphenethyl)acrylamide.
 3. A methodof modifying a taste of a flavored article the method comprising: addingto the flavored article the taste-modifying composition of claim 1.